تفاعل #74710

معادلة التفاعل

phosphorous diphenyl ester

p-nitrophenol

Z-Gly

→

glycine p-nitrophenyl ester

المردود 75.0%

المذيبات

pyridine

pyridine

pyridine

pyridine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONA mixture of 2.93 g
2. 2
   أخرىthe mixture was further reacted for 1 hour
3. 3
   workup.ADDITIONTo the reaction mixture were added 2.61 g
4. 4
   درجة الحرارةunder reflux for 1 hour
5. 5
   أخرىwas removed by distillation under reduced pressure
6. 6
   استخلاصthe residue was extracted with 100 ml
7. 7
   غسيلThe ethyl acetate layer was washed with 2 N
8. 8
   تجفيفHCl, a saturated aqueous NaHCO3 solution and water in this order and then dried over anhydroush Na2SO4
9. 9
   أخرىethyl acetate was removed by distillation under reduced pressure
10. 10
    أخرىto form a solid, which
11. 11
    أخرىwas then recrystallized from ethanol

الإجراء التجريبي

A mixture of 2.93 g. (0.0125 mole) of phosphorous diphenyl ester and 3.37 g. (0.0125 mole) of mercuric chloride was refluxed for 1 hour in 20 ml. of pyridine. Thereafter, 1.74 g. (0.0125 mole) of p-nitrophenol and 10 ml. of pyridine were added, and the mixture was further reacted for 1 hour. To the reaction mixture were added 2.61 g. (0.0125 mole) of Z-Gly.OH having an amino group protected with Z and 10 ml. of pyridine, and the mixture was reacted under reflux for 1 hour. After completion of the reaction, pyridine was removed by distillation under reduced pressure, and the residue was extracted with 100 ml. of ethyl acetate. The ethyl acetate layer was washed with 2 N--HCl, a saturated aqueous NaHCO3 solution and water in this order and then dried over anhydroush Na2SO4, and thereafter ethyl acetate was removed by distillation under reduced pressure. The resulting residue was allowed to stand to form a solid, which was then recrystallized from ethanol to obtain N-benzyloxycarbony glycine p-nitrophenyl ester (hereinafter represented by ##STR9## in a yield of 75% (3.0 g.).

المصدر